From Debtor To Millionaire: How A Windfall Changed My Life

From Debtor To Millionaire is a guest post from J.D. Roth, who founded the blog Get Rich Slowly in 2006 and is the author of Your Money: The Missing Manual. I first met JD in 2010 for lunch up in Portland when I was still working.

By that time, J.D. was already a mini-celebrity in the personal finance world through his story telling abilities and topical focus of paying down debt and living a more frugal lifestyle. We came from opposite ends of the financial and topical spectrum, but as fate would have it, we're in pretty similar boats now.

I admire J.D. because he is a “blogging purist” – someone who writes for the love of writing first, community second, and income a distant third. This is th way I've sought to write all my posts on Financial Samurai since 2009.

Instead of an interview, I asked J.D. to share his story of how he went from debtor living paycheck-to-paycheck to financially free in just a few short years. 

In The Beginning – A Debtor

I'm a lucky man, and I know it. But for a long time, it sure didn't seem that way.

When I was a boy, my family was poor. We lived in a single-wide trailer house in rural Oregon. My father was often out of work. When he was unemployed, things were rough. We never went hungry, but sometimes we came close. More than once, we were bailed out by the kindness of other families in our church.

We didn't always struggle. Sometimes my parents had money, at least for a little while. You see, my father was a serial entrepreneur. He was always starting businesses. Even when he had a job selling boxes or staplers or candy bars, he had something going on the side. Most of his businesses failed, but some succeeded.

In 1977, my father sold one business for $300,000. He was supposed to receive $5000 per month for fifteen years, which seemed like a lot of money at the time. To celebrate, he went out and bought an airplane, a sailboat, and a Kenwood stereo. Life was good — until the buyer went bankrupt. Because he hadn't saved anything from the few payments, Dad was broke again. And unemployed. And a debtor. We were right back where we'd started.

This “famine or feast” pattern continued throughout my entire childhood. Most of the time, it was famine — not feast.

In the late 1980s, I went away to college. Because I knew my parents couldn't help me pay for school, I took care of things myself. I was a good student with a lot of extracurricular activities: president of the computer club, national competitor in Future Business Leaders of America, editor of the school literary magazine, and so on. Plus I had terrific scores on the the PSAT and SAT. As a result, I earned a full-ride scholarship. I worked two or three or five jobs to pay for housing and to earn spending money.

During college, I developed a spending habit. In order to keep up with my friends, many of whom seemed to be rich (as I defined it at the time), I used credit cards. I began to carry debt. At first, I only owed a few hundred dollars, but by the time I graduated with a psychology degree, I had a few thousand dollars in credit-card debt.

After college, my debts continued to mount. I bought a new car. When I had money, I spent it. When I didn't have money, I still spent it. By the middle of 1995, just four years after I'd graduated, I'd accumulated over $20,000 in credit-card debt. It got worse. In 2004, my consumer debt topped $35,000. I felt like I was drowning as a debtor.

Getting Rich Quickly – Goodbye Debtor Status

One night in October 2004, after I’d bounced yet another check and missed yet another payment, I reached rock bottom as a debtor. I began to wonder why I didn’t use my entrepreneurial skills at home.

I was helping to manage the family box factory, and I'd started a computer consulting firm on the side. Both businesses made money, and I made smart decisions with the profit. But at home, my money situation seemed dire.

I asked myself: What if I made decisions in my personal life as if I were making them for a business? What if I installed myself as CFO of JD, Inc? How would I cut costs? How would I increase revenue? Where were the best places for me to direct my cash flow?

That night, I drafted a three-year plan to get out of debt. I didn't want to b a debtor anymore.According to my calculations, I could pay off everything I owed by December 2007 — if I managed my money wisely. I decided to give it a shot.

From debtor to millionaire

I cut back on spending. I boosted my income. As JD, Inc. became profitable and my cash flow improved, I paid down debt. I tracked my spending and created monthly reports to document my progress.

Along the way, I documented my progress on my blog, Get Rich Slowly. There, I fostered an audience of like-minded people and we shared tips and tricks for getting out of debt and building wealth.

The results were remarkable.

In less than a year, I had set aside a $5,000 emergency fund with my wife and had increased my cash flow by $750 per month. I plowed that “profit” into debt- reduction. I continued to manage my life as a business, and in December 2007 — right on schedule! — I became debt-free for the first time in my adult life. No more debtor life!

But it didn't stop there.

I had started Get Rich Slowly on a lark. It had been meant to be a hobby, a place I could earn a few extra bucks while helping myself and others make smarter decisions with money.

The site quickly grew to become something much, much more. By the summer of 2007 — just a year after I'd started the blog — it was clear that this could be a full-time business. I quit my day job to write full time.

As the blog's income grew rapidly — $5,000 a month! $10,000 a month! To much, much more a month! — I began to panic. Remember how recently the creator of Flappy Bird pulled his game off the market after it began to earn $50,000 a day?

Nobody understood him. I did. I remembered the pressure I felt in 2008 and 2009. I hadn't asked for so much money or public scrutiny. I'd simply wanted to write a blog about money and not being a debtor. I was mentally unprepared for the financial success.

Related: How Much Can You Make Blogging For A Living?

I was getting rich quickly, but it wasn't any fun.

I put a lot of pressure on myself to produce quality content every day — twice a day, if possible. Meanwhile, I'd grown fat. I was fifty pounds overweight.

And my marriage was struggling. (I was a dick to my wife and she wasn't very nice to me either.) And then my best friend committed suicide.

In early 2009, I decided to sell Get Rich Slowly. After entertaining a couple of quick offers, I walked away in April 2009, just three years after I'd begun. (Except that I didn't really walk away. I stuck around for another three years acting as editor and primary author. I couldn't tear myself away!)

By selling the site, I received a huge windfall. It wasn't nearly as much as some people have imagined, but it was plenty. It was enough. Coupled with the cash I'd earned over the three years of running the site, my wife and I were millionaires. The debtor life was no more.

Coping With Sudden Wealth

How did it feel going from living paycheck to paycheck as a debtor to having a million dollars in the bank? How did financial freedom change me? The answers to these questions are complex.

The first thing to understand is how fortunate I was to have experienced this windfall after getting out of debt and adopting a new financial blueprint.

If this money had fallen into my lap just five years before, I'd have effed things up. With the “famine or feast” mentality that dominated the first forty years of my life, I would have burned through the money quickly.

Instead, I was smart. Yes, I did spend some of the cash on fun things. I bought a used Mini Cooper. (My quest to purchase a Cooper had become a long-running joke at Get Rich Slowly.) I bought some nice furniture. My wife and I took a trip to Europe. We paid off our mortgage.

But mostly, I ignored the cash. We opened an account at Fidelity and funded a portfolio comprising 60% stock-market index funds and 40% municipal bonds. (This was at the bottom of the market crash, so we were very conservative. In retrospect, this would have been a great time to go 100% stocks, but I still had some learning to do.)

For many people, having a million bucks would be a license to spend. Or to retire. And at one time, it would have been the same for me. But after reading and writing about money for so long, I had a different perspective as past debtor.

My wife and I weren't profligate, but we enjoyed a comfortable adult lifestyle. We weren't willing to make many more sacrifices than we already had. As a result, I figured we had enough money in the bank to retire — at normal retirement age. But we still needed to work to cover our current expenses. 

See: What To Do With A Financial Windfall

It was a tremendous relief to not have to think about the future anymore, but I still needed to focus on earning enough to cover the things I wanted to do in the near future.

More Than Money

I'd be lying if I said that becoming a millionaire didn't change me. It did change me. I'm not sure what my friends and family would say, but from my perspective, these changes have been positive. And they can be traced to one core characteristic: the ability and willingness to try new things and become somebody different.

When I was living paycheck to paycheck, I felt trapped. When I was a debtor, I felt like a slave chained to my job, my home, and my life. I couldn't do anything risky because I had to make enough to pay my creditors.

Once I repaid my debts, those chains were broken. Being a debtor sucked. I achieved a certain level of financial freedom. The more money I had in the bank, the greater that freedom became.

Eventually — when I had a large emergency fund and the blog was earning about $5,000 per month — I felt free enough to quit my day job, which was a huge relief.

Money Gave Me Confidence

As I dug out of debt and built wealth, I also found confidence. I used to be timid and afraid. For a variety of reasons, I was unwilling to try new things. But running Get Rich Slowly fostered confidence and self-esteem. Among other things:

  • I joined a gym and began to eat right, which allowed me to lose fifty pounds and become fit for the first time in my adult life.
  • I wrote a book called Your Money: The Missing Manual, which collected everything I'd learned about money.
  • I began to travel the world. Sometimes I traveled on my own. In the past, this would have been frightening for me. Now I found it exhilarating.
  • I learned to speak Spanish. To ride a motorcycle. To play guitar. And many other things.

I started to see that the primary reason I was chronically unhappy was that I lived my life trying to please others, trying to do what I thought they wanted me to do. Boy, was that dumb. No matter how hard I tried, I could rarely please the people around me. And I certainly couldn't please everyone (which was what I'd been trying to do!). Worst of all, when I tried to please others instead of pleasing myself, I was miserable.

What It Means To Be Truly Rich

“To be truly rich, regardless of his fortune or lack of it, a man must live by his own values. If those values are not personally meaningful, then no amount of money gained can hide the emptiness of life without them.” — John Paul Getty, How to Be Rich (1961)

This realization led to some difficult decisions. As I hinted at earlier in this article, my marriage had gone sour. This was largely my fault, and I own it. I effed up. I wasn't a good husband.

So that we could both be happy, I asked my wife for a divorce. We kept it as amicable as possible. (Now, nearly three years later, we've been able to retain a friendship. We're both dating new people and are much happier than before.)

This newfound confidence and courage to be true to myself didn't come from the windfall. But the windfall allowed me to take risks that otherwise might have seemed too extreme. In a very real way, financial freedom gave me personal freedom.

And you know what? I'm not the only one. Last summer, I participated in a week-long retreat in Ecuador. A group of 25 people gathered to talk about personal and financial freedom. Some of these folks were young and still had debt.

But many had achieved Financial Independence and had net worths of two or five or ten million dollars. Without fail, the folks with money said that the best part of being rich was the freedom it granted.

They didn't buy fancy cars or wear flashy clothes. In daily life, you'd never know these folks had money. They practiced what Sam calls “Stealth Wealth“. Instead, their money provided freedom. (If they did choose to lead a flashy lifestyle, they would have lost this freedom. In theory, a million bucks can fund a $40,000-per-year lifestyle indefinitely; but a $140,000-per-year lifestyle will drain the funds in a decade.)

How Much Money Is Enough?

People often ask me how much money is “enough”. There's no one answer to that question. I know being a debtor sucks. Money isn't the issue. It's expectations that define how much is enough. There are happy millionaires and there are happy people who have nothing.

Happiness is determined by the difference between what you have and what you want. If your expectations (or desires) are greater than your reality, you'll be unhappy. But if you have more than you want or need, you'll be fine. This reminds me of Dickens' Mr. Micawber, who said:

Annual income twenty pounds, annual expenditure nineteen nineteen and six, result happiness. Annual income twenty pounds, annual expenditure twenty pounds ought and six, result misery.

The challenge then is to be content with what you have. This means you have to stop comparing yourself to external measures, such as what your friends and family have, or what society says you ought to have. Who cares? Figure out what's important to you and pursue it.

To be honest, I'm happiest when I have the least: when I'm traveling. I have a backpack of things, and that's it. That's when I'm happiest.

“By wishing to be what he calls ‘up-to-date' as his friends or boon companions, many a young man mortgages his future.” — Orison Swett Marden, The Young Man Entering Business (1903)

The Stealth-Wealth Movement

The millionaires I know personally don't flaunt their wealth. They live in average homes and drive average cars. They wear average clothes and have average jobs.

Again, much of this is because maintaining a modest lifestyle allows the wealthy to keep their wealth. But part of this “Stealth Wealth” is because we Americans don't take kindly to people who have money.

Doesn't that seem crazy? We're a society built on the idea that a person can pull himself up by his bootstraps and become a millionaire. It's a part of our national mythology. But for whatever reason, when somebody actually does this, we resent their success.

I've seen this in my own life – from debtor to millionaire.

During the past decade, I've shared my progress at Get Rich Slowly. At first, readers were on my side. My struggle to get out of debt was relatable.

But the more successful I became, the less others could identify with my situation. When readers learned how much money I made from my site, they became less supportive. And when I sold the blog there were plenty of folks who found this something to condemn rather than praise. (people didn't like seeing a debtor sell out).

For myself, I've decided that I cannot judge a person for being rich. (Well, okay, sometimes I judge, but I try not to do so often.) I've communicated with many wealthy blog readers and chatted with plenty of flush folks in real life.

Most of the rich I know have built their wealth slowly, through hard work and smart choices. They don't flaunt it. They fly under the radar by intentionally choosing to act and appear average.

My point is that in most cases, you don't know how a person has achieved their lifestyle. It may be that the guy down the street with the large house and the fancy sports car financed that stuff on mountains of debt. Or it could be that he has scrimped and saved, or has worked long hours to build a business, in order to afford these things.

Love-Hate Relationship With Money

I've written before about America's love-hate relationship with wealth. You can clearly see this in the way we self-identify. Nobody wants to say they're rich.

But if you make $100,000 a year, you are rich. Not just by world standards, but by American standards. (The median household income in the U.S. between 2008 and 2012 was $53,046. Now it is $68,000 in 2021.

That means half the population earned less than that and half the population earned more.) I'd argue that if your family brings in more than $75,000 per year, you're rich. But few people seem to agree.

I'm not condemning anyone for being rich. I founded a site called Get Rich Slowly, after all, and my aim is to help people destroy debt and build wealth. To me, wealth is a noble aim, especially if it's used to improve your life — and the lives of others.

I don't believe that wealth corrupts or that it attracts bad people. (It might, however, magnify your personality; if you're already an asshole debtor, having lots of money might make you more of an asshole debtor.)

I'm not saying that every rich person deserves to be so, and I'm not saying that we should move to a socialist society. I'm just puzzled why we simultaneously love and loathe the wealthy. Is this healthy? Is it normal?

Taking the Red Pill

Instead of vilifying those who have become rich, I think more people ought to profit from listening to what they have to say. If you take the time to ask questions, they'll tell you how the got what they have — and how they keep it. They'll tell you how they think others can do the same.

From my experience, most millionaires will say that wealth comes from spending less than you earn — from saving. And extreme wealth comes from extreme saving. The greater the gap between what you earn and what you spend, the more you can save.

For some millionaires, this means earning a lot of money. For others — like my “real millionaire next door” — it means cutting costs drastically. For most, it's a balance between earning and spending.

Most people don't take this advice seriously. They don't understand just how important it is. In truth, this is the only thing you really need to know about personal finance. Do this, and you'll build wealth. And the bigger the gap between your earning and spending, the wealthier you'll become.

No More Excuses

People also like to make excuses. “That's great,” they say, “but it doesn't apply to me because of X.” I'm sorry, but it does apply to you. And as long as you make excuses as to why it doesn't or why you can't follow the advice, you're not going to get ahead. End of story. It's nothing personal. It's just math.

If you want the math to work in your favor, you have to take charge. You can't be a victim. Your situation may not be your fault, but it's your responsibility to improve it — nobody else's. (See: Why Not Just Try Harder To Get Ahead?)

Another barrier is that many folks aren't willing to make short-term sacrifices for long-term freedom. They don't understand what financial independence actually means and what it feels like. So, they numb themselves with consumption and call it good enough. They're complacent. They don't realize that if they buckled down for a few years, they could escape the entire system.

Look, it's like The Matrix. There's a pleasant pattern to our society, and it's tough to see outside of it. But trust me, there are plenty of people who have taken the red pill, who have stripped the blinders from their eyes. Once you step outside the Matrix, it's easy to see how it works, how you once were manipulated, how most people continue to be manipulated.

Financial Independence

To escape, you've got to listen to what the quiet millionaires are whispering. Take your advice from the folks who have been successful, and not from those with flash and bling but nothing to back it up.

“Many a man is poor today, although he has worked like a slave, simply because he could not save.” — Orison Swett Marden, The Young Man Entering Business (1903)

I'll end this long article where I began it: I'm a lucky man, and I know it. I've worked hard to get what I have, but many other people have worked harder and have less. And if my windfall had occurred any earlier, I probably would have squandered the money. Instead, it came at a time when I was ready and able to be smart with money. My challenge now is to grow this nest egg.

In the meantime, I'll do what I can to keep preaching the gospel of Get Rich Slowly. Don't be a debtor any more.

Update 2024: JD first wrote this guest post in 2014 and has since reacquired GRS from the original buyers for a nice discount. That's a huge win because one you sell your baby, it's very hard, if not impossible to buy it back. However, in this low interest rate environment, you never want to sell your cash cows!

Unfortunately, JD says he only has $200,000 left and is feeling some financial stress. He says he needs to find a way to make more money from GRS.

Related posts:

Things To Consider Before Selling Your Business

Why I'll Always Regret Selling My Business For Millions Of Dollars

47 thoughts on “From Debtor To Millionaire: How A Windfall Changed My Life”

  1. I love this. It took me a while but I’m finally here. I have learned all the things you learned these past two years. Freedom does come at a cost and it’s unlearning all the things I’ve been taught as a young girl and as a woman. I drive a car that is paid for but still handles beautifully in the snow and has heated seats and lumbar support. It’s kept me safe in two accidents and still it affords me more than transportation–I owe nothing and I’m not a slave to the lender. I have a nice savings account. I’m not rich but I’m slowly building. I travel more than I’ve ever traveled and yes, sometimes by myself as well. I recently schlepped through Mexico which scared me. I would rather live low and owe little than to live opulently and worry if I can keep it. I spend my days seeing things I could have if I wanted it but smiling to myself when I have learned the greatest lesson of all, nothing is worth stress and losing sleep over and peace is the most valuable state of being than anything money can buy and my savings and no debt has afforded me that. I can’t tell you how many times I’m asked why I don’t get a new car and the latest was a married attorney friend expressing his concerns to his wife and me that I needed to find a man to settle down with because I was not getting any younger and I could be taken care of by anyone if I wanted it and that I should be thinking like that. I like my life right now. I appreciate your words. I saw myself in much of it.

  2. I read mark Ferguson ‘s blog every other week.. Something that I want to do also…

    While mark probably makes over 600k a year… I may start making 400-500k soon, by 2015-2016 year.

  3. Awesome! I’m on my way to being debt free in 2 weeks. I’m hoping to be one of those who go from rags to riches. I’m in a stable job making over $150k a year, but I know that won’t allow me to be financially free.

  4. J.D.,

    It’s interesting to read that some of your supposedly-loyal readers suddenly despised your hard-earned wealth. I agree with what Mark Ferguson stated. You can’t please everyone. The readers that turned on you would love to have been in your shoes when you sold Get Rich Slowly. Keep sharing your knowledge and story which is inspiring to me. I hope you continue to profit!


    1. We are social creatures. When we find something we identify with, we want to see it do well, but no so well that we feel excluded or no longer can relate. Regardless of rationalizations, JD’s ability to quit his day job, then selling of the blog, all put him in an area where many likely felt they could no longer relate to him. Can’t relate, you tend to feel threatened, then you feel betrayed, then you focus on the differences rather than the similarities and then you vent.

      1. As one of the dwindling numbers of Americans who will have a pension when I retire, I feel the same thing. For some reason, those without pensions feel that if they don’t have one, nobody should — it’s been dubbed “pension envy” by some. A pension is simply deferred compensation, i.e., it’s forced savings from what would otherwise be a larger paycheck for me.

  5. Great interview Sam and thanks for being that honest JD..

    It is really enlightening to hear that money is not always all that it is cracked up to be and the importance of preparing yourself for what your life will look like after the “windfall”..

    Would you say that your success was built on a lot of hard work and being in the right place at the right time?

  6. Get Rich Slowly is one of the first PF blogs I started reading in 2009. It inspired me to get my act together. Though I’m still working out all the kinks, I’ve found my path to actually meeting my finance goals. I also love his analogy of the Matrix – once you can step outside of the pattern of our society, you can actually see how it all works and it boils down to saving more than you earn!

  7. As everybody have already said: inspiring post….
    Currently, building up the emergency fund and captial…
    Wish to do what Rober Kiyosaki advices: Keep up the day job and mind your own business
    And like JD’s minicooper, I wish to have Beatle….
    Let us see.

  8. This is a classic example of why being an entrepreneur puts the odds in your favor of accumulating wealth quickly. This is why doesn’t paint the entire picture of the actual benefits of being an entrepreneur, I explained a lot of the true benefits in the comments. As an entrepreneur, not only do you have more control on how much income you make (can you imagine how long it would have taken you to replace your blog income with a job?) but you can also sell your asset for a ton of money and get a “windfall” someday.

    Congrats man! I hope that this story inspires others to become entrepreneurs.

  9. Life After FI

    Enjoyed the post…….. I have been reading J.D’s post since long! Good to know that both of you know each other… small world!

  10. Thank you for sharing your story. I must say I am amazed at how well that blog did. Kudos to you. Sorry to hear that money may have been a factor (if not the driving one) in your personal relationship. It seems like it is always a factor somehow.

  11. I have personally found that people start losing compassion for your financial situation if they know you earn over 100K per year. I don’t know why that seems to be the cut-off, but it happens time and time again. At the 100K mark, many consider you to be filthy rich and somewhat insulated from everything else that’s going on in the world.
    This really confuses me, but I believe I have a skewed perception of wealth since I live in an affluent part of the country and rarely encounter poverty of any kind.

    1. Holly – I’ve also found the same thing. I think this perception resonates with the generation before (our parents). $100k in 1975, 1980, and 1985 has the relative buying power of $439k, $287k, and $220k in 2014, respectively. I just think this was a notion passed down which is easily relatable to as “6-figures” is a concrete figure people can visualize. I do agree with you that in 2014 this perception has to be adjusted due to the increase in cost of living over the period, and $100k might have once been “rich” but is no longer the case.

    2. I think in general, regardless of income, most people tend to think someone making two to three times more than they are has nothing to really complain about, while someone making five times more than they are, is rich.

      So to someone earning the median family income of about $50K I think they would tend to lose sympathy for someone making over $100K with respect to money issues.

      Similarly, someone earning $100K is likely to lose sympathy for someone earning over $200K.

      So to someone who is only making $20-25K a year someone earning over $100K is rich and should have no money issues and is considered rolling in it. It’s this kind of earning disparity that can cause issues between siblings and among family and is frankly one reason I don’t disclose how much I make or how much I’ve saved to my or my wife’s immediate family.

  12. Stefanie @ The Broke and Beautiful Life

    Financial Freedom = Personal Freedom. I love that. It’s so very true. Thank you for sharing this. I’ve read Get Rich Slowly since I started blogging two years ago and it’s so interesting to hear all the backstory.

  13. Wonderful story! Congratulations on your success.

    A household income of $100,000/year is rich, at least statistically. But, if you live in a high cost metropolitan area, you will be very financially challenged.

  14. No Nonsense Landlord

    Definitely an inspiration. There are so many rags to riches stories out there. It takes drive, motivation and ambition to make it.

  15. Great story! I am always interested how people succeed. I am always surprised how people need to go through tragedy or some low point to change though. I admittedly never had a significant low point to inspire me to achieve. I am a lifelong saver and planner who achieved financial independence in my late thirties. Afterwards, I started some businesses and cashed out. For the last 29 years, I picked jobs/careers that I enjoy. This is real freedom!

  16. Very nice article.

    Out of curiosity is a million dollars in investible funds still considered the/a tipping point from which you could achieve financial freedom (lets say for someone who has no consumer debt and owns their own home)? I know that other sites are talking about doing it with even just $500K but that seems like a bit too restricted a lifestyle for me anyway.

    Starting to get VERY close to that point. It isn’t when I plan to retire as I expect I will probably continue to work for many years but I am very much looking forward being able to head in to work knowing that should the worst happen I will be just fine. In the meantime I just plan to reel in expenses as much as possible to find that comfortable but reasonable budget living point so I know that I will be happy and successful in a lower income lifestyle.

    1. David, there’s no one “tipping point” for financial freedom. For one person, freedom might come at $100,000. For another, $10,000,000 might not be enough. It depends on your lifestyle, on how much you spend.

      As I mention in the Get Rich Slowly course, I use a general rule of thumb when discussing whether or not somebody is financially independent. It goes something like this:

      Compute your average annual spending. Also compute your liquid assets (including investments and retirement funds). Now divide your assets by your annual spending. This magic number would be called a “liquidity ratio” in business (and be measured in months not years). If the number is .5, that means you’ve saved enough to cover six months worth of living expenses. If it’s 3, you’ve saved enough to cover three years of expenses.

      GENERALLY speaking, making standard assumptions about investment returns and safe withdrawal rates and inflation, most folks can retire (have reached financial independence) when this number reaches 25. If you’re timid or make conservative assumptions, you should wait until the number reaches 30. If you’re bold or make generous assumptions, you might say you’re ready once the number is 20.

      That said, there’s no reason you *have to* wait that long to quit your day job. I’d argue that many more people should be waving good-bye to regular work when they’ve saved enough to cover ten years of expenses. Take some time to explore yourself and explore the world. Experiment. Try new things. Take some risks. Sure, you’ll burn through some of that money, but I’m also willing to wager you’ll learn a lot more about yourself and probably find yourself a year or two down the road doing something you love even more — and earning an income at the same time.

  17. JD is awesome, his site is where I originally got hooked on personal finance blogs after college. Still utilize the forums from time-to-time today.

  18. This article could not have hit closer to home for me right now. I’ve been blessed by being “lucky” by working my butt off, saving 70% of my income, being debt free, investing wisely…now I’m faced with a similar situation as you. The only difference is that my “walk away #” was already banked a few years ago, and now there is an opportunity for a transition that will let me start the next chapter and just add to the already comfortable cushion. The challenge I’m facing is, damn I’m only in my early 40’s and still love what I do…well I’m sure I’ll be able to figure that out. I don’t want to allow myself to simply have lifestyle inflation because I’m continuing to work and the money rolls in…honestly over a certain number, you have to work to spend that much money…and if you are spending over that amount, you have a spending problem IMO. Life lived well is actually pretty cheap and like you JD, I’ve been the happiest when I am traveling, exercising, and taking the time to smell the roses. The next few months are going to be pretty interesting for me…thanks for writing this article, it really helped reading about your situation and journey to where you are at today.

    1. I’m curious what that number is, the number above which one has to work to spend it, care to share?

      Obviously that number is going to be different for everyone and in every location, but I think it would be an interesting point to discuss or think about.


      1. Ah yes the number…well for me that number, that if you “have” to spend more than to get enjoyment out of your life, is $20,000/month after taxes. I will hear people say that oh, it’s all relative and if I live in NYC I couldn’t do that…well I’ve traveled the world and yes NYC and similar cities are great, but there are equally great places to live that offer as much if not more and are far less expensive. I could live like a king on half of that, and I think that’s where I agree whole heartedly with you that you’ve got to be able to be happy with what you do have.

        The number you have to save to walk away once again is different for everybody…I am more conservative than others and I use the 33 rule of thumb…basically my savings needs to be 33 times my annual burn. With a proper investment plan, you should have nearly a 100% probability of never outliving your $.


    2. “Life lived well is pretty cheap”…well said! I have to remind myself this statement every day.

  19. Pura Vida Nick

    Very inspiring article. What resonates with me, at this point in my life, is being happy with what I have. We have it ingrained in us from a young age that we are competing and comparing with other people. But as you said, when you tried to make others happy (AKA comparing and caring what others think) you yourself became UN-happy.

    I also love reading posts by Sam and JD because you guys are already financially independent. I wish to be FI, so I like to get glimpses into your lives. But I am working hard on being content now, with my journey, even while striving for a different future. I don’t want to get FI but have bad habits, a bad personality, or some other new goal after FI that keeps me always striving. I want to sit and enjoy the marrow of life, both now and after FI.

    1. When you look back, it’s really the journey that’s the most rewarding. It’s nice to have some money to be FI, but it’s really about the freedom to choose that’s terrific.

  20. SavvyFinancialLatina

    It’s very inspirational. I agree having financial security makes your life happier. I’m not saying money makes you happy, but the security of knowing your bills are going to be paid causes less stress. For example, my husband did not get paid well on a job he did. While it upset me greatly, mostly at the people who failed to pay him, I did not get mad at him, and I did not worry about paying bills, since we have savings. But I understand if it had been 2 years ago, I would have been so stressed and mad since we were living paycheck to paycheck. We want to live a low key, modest life. I’m hoping if we continue to save and invest diligently, we won’t be tied to our slave jobs till we die.

    1. People welching on their agreements annoy me the most. That is so dishonorable.

      It took me 5.5 months to get paid by one vendor once. I couldn’t believe it, and I escalated the situation straight to the top of their multi-thousand organization. I shouldn’t have had to keep asking to get paid for a service done.

  21. The First Million is the Hardest

    Nice post. I started reading GRS in 2008 or so, it’s really one of the main reasons I started my own site. Thanks for sharing your story JD, it’s good to get a little glimpse into the life.

  22. Great post! I agree completely. Most people have an excuse for why the can not save money. I disagree with most of them. Most wealthy people started off the same way we did….not making much money. If you live within your means you can accumulate wealth. It may take a while but it is possible.

  23. Great article! I have some of those fancy things like a big house and nice cars, but before I had those I saved a lot of money. I still save a lot of money and then invest it in real estate to grow it quickly. The key to being wealthy really is saving as much as possible.

    I wonder what your opinion on this would be. You mention wealth gives you freedom, but people’s perception of wealthy people causes some people to “hide” their wealth. Wouldn’t this be an example of the wealthy letting others govern how they live their lives instead of truly being free and buying expensive things I they make them happy? It seems like less freedom of you govern how you live your life by how others perceive wealth.

    I am very open about the money I make on y blog because I think it can be inspiring and that is my goal. I want to reach those that want to make it big, not those that resent people that make it big. Although maybe I can convince a few people it is possible with the write attitude and plan.

    Great job!

    1. Interesting question. I think maybe if your true nature demanded that you buy lavish things for yourself to be happy, and yet you didn’t do it so that you could fly under the radar, then yeah that might cause unhappiness.

      But most of the “stealth wealth” folks I know do this for two reasons.

      First, it lets them live a comfortable life without being harassed by folks around them. I’d much rather appear average and not get shit from anyone than to display my wealth and have to deal with haters.

      But the second reason is because by participating in the “stealth wealth” movement, the wealthy are able to maintain their wealth. Does that make sense? By buying a used Mini Cooper, I save tons of money over buying a new car. I save $15,000, which is enough to fund six months of my current lifestyle. Not a hard choice there, at least not for me: Step down from new car to used car and get to do what I’m doing for another six months. Done!

      1. Thank you J.D. for the reply. My thoughts are based on two of my loves houses and cars. I am a real estate agent and investor and deal with houses all day long. I have a nice house and I saw the exact same thing you talk about with friends and some family really not liking me or my wife have a nice house.

        I would think if wealthy people let other peoples thoughts on their house being too nice affect the perfect house for them they would be letting the haters have way too much control. I have learned to go for what I want and not pay much attention to the haters. You can’t please everyone.

        As far as the saving money thing I get that, I was making that comment assuming buying a nice car or house would not affect savings or lifestyle in anyway. I save a large percentage of my income I don’t every make any purchases that affect they way I live now or in the future. That is also why I tend to invest in cash flowing investments that keep paying me each month and I don’t have to worry about my money running out.

        1. Mark,

          I think it also depends on how much you make.

          If you’re making $10,000-$20,000 a month, it’s probably not that big of a deal, no matter where you are in the country.

          But if you are making say $50,000 a month or more, that starts to get a little crazy given the median household income is around $53,000 a year. You will UNDOUBTEDLY have haters as a result. It just doesn’t feel good anymore.

          It’s much better to just come across as your every day middle class fella.

          How much do you disclose you are making on your site a month?

          1. Mark,
            One of the things that I don’t care for in my current industry is that success is frowned upon by individuals…the whole “you shouldn’t be making that much money”. My outward appearance to my workers/customers/suppliers is about 1/10th of my income. I cannot drive my nice cars to work for fear of what would be said, nobody knows what home I live in…yet I gainfully employ a over 100 families off the back of the ideas and hard work that I’ve put in to create the business into what it is today.

            The interesting dynamic to me is when I say enough is enough, because I am able to live the life I want on so much less and I hang up the spurs, quit paying a ridiculous amount of taxes (IMO)…what the ripple effect will be. I’m pretty sure that the very people who I’m paying $100k + year that would vilify me if I pulled up in an expensive car, will sure the hell want things to go back to the way they were. Yeah, the rich are evil greedy bastards…but they are usually also the ones that are creative, think outside of the box and solve problems instead of just complaining about the problem, have real world people skills, give people good jobs, and typically are generous caring members of the community. O.k. rant over for now : )

          2. Sam, I dot disclose exactly what I make, but people can put the number together if they wanted too. I do disclose I make about $5k a month of my rentals, I disclose I sold 190 house last year as a realtor which equates to over 500k, but I have a lot of staff and team so it’s not all profit. Then I fix and flip 10-15 homes a year and averaged making over 30k a flip last year. A have a few other sources like BPOs and revenue from my blog. I don’t disclose all of it at once but I do disclose I invested almost 300k in cash buying and repairing my rentals the last three years.

            1. The Millionaire Next Door is the bible for stealth wealth

              people are pissed because they sense that wealthy folks are the only ones getting wealthier. People in the top 0.1% with $20 million or more. And they’re right.

              Even people in the top 1% aren’t gaining that much wealth over the decades. So people wealthy with Wealthy who are indeed taking $9 out of every $10 in wealth and income gains.

              the reality is 16,000 families own 6 trillion in assets equal to the bottom ⅔ of American families wealth. The ultra rich are in a class by themselves.

              which leads me to another related point. the world’s 85 richest are now worth as much as the poorest 3.5 billion

              I end with a final macro point. While a certain few here may be doing well, the 99.9% envy is not directed towards you. it’s directed toward knowingly or not against the top 0.01% that are leaving ever smaller breadcrumbs for them (and you).

              Once you understand that r>g where r is the rate of growth of capital gains, and g is the growth in national income, you’ll realize after reading Amazon’s current #1 best seller, an economic tome no less, the magnum opus, Capital in the 21st Century, that capitalism is rigged for wealth concentration that will squeeze the 99.9% into crumbscicles.

              For those who want a real world review and understanding of the bigger picture, read

              People are pissed for good reason because they know they’re getting fleeced. They just don’t know why or how or by whom. So everybody is suspect, and for good reason.

  24. Sam & JD,
    This is a very inspiring post. I read Get Rich Slowly daily and had no idea of the history. I think my favorite part was about the traveling & minimalism. The older I get, the less I feel I need and it’s amazing.
    Keep up the great work!
    P.s. What happened to “Get Fit Slowly”?

    1. Haha. I can’t believe someone here knows about Get Fit Slowly. That blog has a funny story — at least to me.

      I was at lunch one day with my friend Mac. This was a year or two into Get Rich Slowly. Anyhow, we were eating at an all-you-can-eat Chinese buffet and stuffing our faces. “Boy, I’m fat,” I said. “Yeah, me too,” Mac said. Silence. I was just about to tell him my idea for a great new blog — Get Fit Slowly — when he said, “You know, I’ve been thinking about starting a blog called Get Fit Slowly.” Curses! Anyhow, we went in as partners. For about a year, we wrote the blog together. But then Get Rich Slowly blew up and I didn’t have time. So, Mac ran the site for a while before letting fall into the dustbin of history. I think it’s been a year since he last updated it.

      And that’s the story of Get Fit Slowly. :)

      1. Man, Mac shoulda partnered with you in Get Rich Slowly! What does he think now that he knows you sold it for big bucks? Does he at least get a free buffet when you guys meet up?

      2. I just subscribed to your newsletter.

        Just read article “from debtor to millionaire .”

        Very inspired by Get Rich Slowly.
        Equally inspired by Get fit slowly.

        Then a thought enter my mind.

        What about “Get your wife back slowly?” I think a 3 year plan just might work.

        Please pass the word to JD.

        Just me, Wendy

Leave a Comment

Your email address will not be published. Required fields are marked *